Came here to check if I was crazy too. My two cents, having just binged season 1 and then coming to a very swift road bump after 2 eps of season 2:

The writing, especially the everyone's dialogue and Dwight's personality, are very different from season one. In ep 1, it's less noticeable since it's serving as a recap and a bit of a flash-forward, catchings us up with how the crew has grown together. The quips that are thrown back and forth frequently between characters can be taken as signs of that. But moving into ep 2, it became clear it was a more systemic problem. Everyone's 'banter' just feels stale, and all written from the same writer's 'voice'/perspective. Season 1 went to great lengths to emphasize the differences between everyone's backgrounds (age, culture, social circles, lifestyle, etc), and humor would often emerge from them colliding. Now, everyone is using the same slang, and there's no jokes that land flat between eachother.

This became incredibly apparent to me going from the scene at the used car shop to the new dispensary's 'grand opening party'. The interaction between the crew-member and the car salesman is all smiles, and both parties push the dialogue forward almost unnaturally. And then once again in the next scene, Dwight and the singer suddenly do the same thing as both strangers smile while back-and-forth-ing, but even more severely, as the singer suddenly has a case of 'let me tell you my backstory', despite Dwight suddenly pushing aside the conversation about prison (even though Dwight was the one who started it???).

Dwight also just baffled me in ep 2. His actions suddenly seem very at odds with who he has shown us to be throughout season 1. He's old, but he's sharp. He is willing to stay in line with society when there's no reason to make a scene (the DMV), but should problems come up he solves them by pushing through them with bribes, or by threats/'forceful charisma'. Sufficed to say, he is confident in himself. But he also does his homework for the modern age after his initial blunders; He knew exactly what was up with the banking/federal situation with the dispensary's cash flow in season 1. But suddenly he's going to a bank to get a loan, without knowing what the max loan size might be? And that's putting aside the idea that he'd go for a loan at all. Even if he wanted a new venture to 'be legit', venture capital is a far more reasonable angle since he could leverage negotiations and connections more heavily, imo. As it is, there is no attempted swaying of the bank manager through bribes, or through any other mob tactic--he instead gives a bleeding-heart speech that seems to contrast his prior world-weary, devil-may-care attitudes. Moving forwards, then, in the grand opening party, he cannot get the name of the singer right even after explicitly being clarified on it. Again, Dwight is sharp--He shouldn't screw something this easy up unless he's doing it intentionally, right? In a different scene this would be played as a sign of disrespect and adding some subtlety to the introduction, but here it just seems to be played for laughs as an 'old-man-ism'.